Process of manufacturing new organic fatty-acid compounds.



WILLIAM common, on HooHsT-oN-rHn-MA'm, GERMANY,

ASSIGNORS T0 FARBWERKE VORM. MEISTER LUCIUS &: BRfi'NI1\TG, OF HtioHsT-oN- No Drawing.

Specification of Letters Patent. Application filed April 5, 1909. Serial No. 488,007.

Patented Mar. 28, 1911.

To all whom it may concern:

Be it known that we, Ph. D., and WILLIAM COTTON, citizens of the Empire of Germany and the Kingdom of Great Britain and Ireland, respectively, residing at Hiichst on the Main, Germany, have invented certain new and useful Improvements in Processes of Manufacturing New Organic Fatty-Acid Compounds, of which the following is a specification.

According to this invention, by treating unsaturated fatty acids of high molecular weight with aldehydes or ketones, that is to say with neutral compounds containing the carbonyl-group, which renders them capable of combining with phenylhydrazin and hynew chemical compounds are formed which are soluble in alkalis and very stable in the cold. The reaction is carried out with the addition of condensing agents. These new compounds have the surprising, and in practice extremely important, property of reacting when hot like the free fatty acids. This property has led to a valuable new process in alizarin printing. Certain alizarin dyestuffs, such as alizarin-red, alizarinpink and alizarinorange could hitherto only be printed on goods which had previously been prepared with Turkey-red 011 or the like. As this oil preparation is expensive and causes extra labor to the printer, it has already frequently been attempted to simplify the process in various ways. Amon others the addition of Turkey-red oil to t e printing colors has been proposed;- this has, however, proved to be lmpracticable, asin this case the color lake is formed already in the printing color and thus prints are obtained which are not fast. On adding free fatty acids, the formation of the lake in the printing color can be avoided, but the effects obtained are not equal in brightness to the prints on goods which have been previously oiled.

On adding the above-mentioned new compounds of the fatty acids to the printlng color, color lakes are not formed in the printing colors and the latter keep for any length of time. When the prlnted goods are steamed, the fatty compound enters the color lake. J

Besides simplifying the method of working, the new process offers another advantage in that the non-printed parts do not HEINRICH Rossman, I

turn

ketones, acetone is especially suitable. In

the place of the free fatty acids, the respective fats may also be employed; these are partly transformed during the process into the free acids.

The following examples illustrate the invention, but are not intended to limit it in any way.

Examples of the manufacture of the compounds.

1. 1 kilo of ricinoleic acid is stirred with 200 grams of acetone, then 200 grams of concentrated sulfuric acid are gradually run into the mixture while cooling. The mixture is afterward stirred for some hours. The reaction-product is washed by stirring it in a solution of Glauber salt of about 10 per cent. strength, made thinner by heating to 90; t-he'oil is removed and freed from acid and excess of acetone by washing. The oily reaction product is allowed to settle well and the separated water removed.

he quantities of the acetone and acid may be varied.

2. 5 kilos of oleic acid are gradually -mixed first with 750 grams of formaldehyde and then with 1,000 gramsof 40% strength of concentrated sulfuric acid and then treated in the manner'as set forth in Example I. The quantities of the formaldehyde and acid may be varied. a

3. 10 kilos of ricinoleic acid and 2 kilos of formaldehyde of 40% strength are mixed, the mixture saturated with acid and well stirred for some time. free acid isthen washed out and the oily product of the reaction drawn oil. In the place of sulfuric acid-or hydrochloric acid there may be used in this example about 2 kilos of chlorid of zinc.

4. 1 kilo of castor oil is gradually mixed with 250 grams of formaldehyde of 40' per cent. strength at 20 C. and stirred for some time, then 200 grams of concentrated sulfuric acid are added as condensing agent at hydrochloric 2 eeepsa -20 C. and the mixture is allowed to treating ricinoleic acid, in presence of a stand over night. The product of the recondensing agent, with compounds containaction is washed with a solution of Glauber ing the carbonyl-group G0, which renders salt for removing an excess of acid and aldethem capable of combining with phenylhy- 5 hyde, when it separates as a mass like butdrazin and hydroxylamin.

ter. In order to be able to wash this mass 4.. The process of manufacturing new orbetter, it is heated together with the soluganic fatty compounds, which consists in tion of Glauber salt to 90, whereby it is treating unsaturated fatty acids of high made thinly liquid. The quantities of the molecular weight, in presence of a mineral 10 formaldehyde and acid may be varied. In acid, with compounds containing the carthe place of formaldehyde solution the corbonyl-group G0, which renders them caresponding quantity of solid formaldehyde pable of combining with phenylhydrazin may be used. and hydroxylamin.

The reaction-products obtained according 5. The process of manufacturing new or- L5 to the above four examples are light-colored ganic fatty compounds, which consists in oily substances which are thick liquids when treating unsaturated fatty acids of high cold and thin liquids when hot. They are molecular weight, in presence of a condenslighter than water and have a slight aroing agent, with formaldehyde. matic smelL' They cannot be distilled with- 6. As new articles of manufacture, the

20 out being decomposed. They dissolve in dicompounds of an unsaturated fatty acid of lute alkalis and can be separated from the high molecular weight with compounds consolutions by means of acids. As they are taining the carbonyl-group G0, which rennot quite insoluble in water, the separation ders them capable of combining with phenylmust be effected in presence of Glauber salt. hydrazin and hydroxylamin, said com- 25 common salt, ammonium sulfate or the like. pounds being light-colored oily substances hey are soluble in most of the organic which are thick liquids when cold and thin solvents. The said products are suitable liquids when hot, lighter than water, having for use in alizarin printing. a slight aromatic smell, dissolving in dilute Having now particularly described our alkalis and in most of the organic solvents, 30 invention what we claim is: and being suitable for use in a-lizarin print- 1. The process of manufacturing new oring. ganic fatty compounds, which consists in treating unsaturated fatty-acid bodies of compound of ricinoleic acid with formaldehigh molecular weight, in presence of a hyde, being a light-colored oily substance 35 condensing agent with compounds containwhich is a thick liquid when cold and a ing the carbonyl-group G0, which renders thin liquid when hot, lighter than water,

7. As a new article of manufacture, the

them capable of combining with phenylhyhaving a slight aromatic smell, dissolving drazin and hydroxylamin. in dilute alkalis and in most of the or. 2. The process of manufacturing new or- 1 ganic solvents, and being suitable for use in 40 ganic fatty compounds, which consists in alizarin printing.

treating unsaturated fatty acids of high In testimony whereof, we affix our signamolecular weight, in presence of a condenstures in presence of two witnesses.

\ l I ing agent, with a body containing the carbonyl-group G0, which renders them ca- 45 pable of combining with phenylhydrazin and hydroxylamin.

3. The process of manufacturing new or- 1 ganic fatty compounds, which consists in Witnesses:

JEAN GRUND, CARL Gianni). 

